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Updated: Apr 8, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Nickel-Catalyzed Insertion of Alkynes and Electron-Deficient Olefins into Unactivated sp(3) C-H Bonds
Soham Maity1, Soumitra Agasti1, Arif Mahammad Earsad1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076 (India).
Abstract:
Insertion of unsaturated systems such as alkynes and olefins into unactivated sp(3) C-H bonds remains an unexplored problem. We herein address this issue by successfully incorporating a wide variety of functionalized alkynes and electron-deficient olefins into the unactivated sp(3) C-H bond of pivalic acid derivatives with excellent syn- and linear- selectivity. A strongly chelating 8-aminoquinoline directing group proved beneficial for these insertion reactions, while an air-stable and inexpensive Ni(II) salt has been employed as the active catalyst.
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